Diamond Head Oahu

Oahu Vacation Packages

 
Oahu, "The Gathering Place", is home to Honolulu, Hawaii's largest city. Iconic Waikiki dazzles with its classic beaches, exciting nightlife and world-class cusine. On the northen side of the island, the surfer's paradise of North Shore, home of the Banzi pipeline and scenic rainforests offers a laid back island style visitors are sure to enjoy. To the West, Pearl Harbor is steeped in history with its WWII memorials and massive ships. Throughout the island a fusion of asian, polynesian and western culture give Oahu a flavor all its own. Enjoy the best Oahu deals on Hawaii vacation packages today!
FREE 3-Day Midsize Hertz Car Rental
  • Minimum 3-night vacation packages
  • Book by 3/1/20 for travel through 12/14/20
All Deals Include: Round-trip flights, hotel accommodations, taxes and more
  • Aston Waikiki Beach Hotel
    Aston Waikiki Beach Hotel
    Waikiki, Oahu Our 4-Star classification designates those properties with well-appointed, deluxe accommodations, extensive amenities and comprehensive guest services. Expect attention to detail and a warm and hospitable staff ready to cater to your needs. These superb properties offer a truly refined getaway.

    From its urban-Hawaiian beach theme to its vibrant tropical colors and unique decor, this hotel across from Waikiki Beach is fun and full of life.

    • City View King
    • Includes EXCLUSIVE 3-Day FREE mid-size car rental

    3 nights with flight from $538+

    Portland, Oregon (PDX) departures, valid for travel 03/02/20 - 03/05/20
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  • OHANA Waikiki East by Outrigger
    OHANA Waikiki East by Outrigger
    Waikiki, Oahu Our 3-Star classification designates those properties where guests experience an ideal mix of comfortable accommodations and modern amenities. Most of these hotels feature a variety of services, and offer distinguished style and comfort.

    Discover the exceptional value of every stay at OHANA Waikiki East by Outrigger, set in the midst of the city's dynamic cultural scene, just five minutes from the beach and within walking distance of virtually every conceivable type of activity.

    • Corner Queen
    • Includes EXCLUSIVE 3-Day FREE mid-size car rental

    3 nights with flight from $610+

    Portland, Oregon (PDX) departures, valid for travel 03/02/20 - 03/05/20
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  • Hyatt Regency Waikiki Beach Resort and Spa
    Hyatt Regency Waikiki Beach Resort and Spa
    Waikiki, Oahu Our 4.5-Star classification designates those properties with well-appointed, deluxe accommodations, extensive amenities and comprehensive guest services. Expect attention to detail and a warm and hospitable staff ready to cater to your needs. These superb properties offer a truly refined getaway. Half star indicates that the hotel/resort meets all criteria of the designated rating and exceeds in certain areas.

    Explore the excitement of Oahu in one of Hawaii’s most fashionable zip codes. Just steps from renowned warm waters and spectacular views.

    • Waikiki City View King
    • Includes EXCLUSIVE 3-Day FREE mid-size car rental

    3 nights with flight from $639+

    Portland, Oregon (PDX) departures, valid for travel 03/02/20 - 03/05/20
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  • Hilton Hawaiian Village Waikiki Beach Resort
    Hilton Hawaiian Village Waikiki Beach Resort
    Waikiki, Oahu Our 4.5-Star classification designates those properties with well-appointed, deluxe accommodations, extensive amenities and comprehensive guest services. Expect attention to detail and a warm and hospitable staff ready to cater to your needs. These superb properties offer a truly refined getaway. Half star indicates that the hotel/resort meets all criteria of the designated rating and exceeds in certain areas.

    Lush grounds, six spectacular pools, a beachfront lagoon, waterfalls and an array of shops and restaurants are all part of the "Village" experience at this expansive resort.

    • Resort View
    • Includes EXCLUSIVE 3-Day FREE mid-size car rental

    3 nights with flight from $654+

    Portland, Oregon (PDX) departures, valid for travel 03/02/20 - 03/05/20
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  • Sheraton Princess Kaiulani
    Sheraton Princess Kaiulani
    Waikiki, Oahu Our 3-Star classification designates those properties where guests experience an ideal mix of comfortable accommodations and modern amenities. Most of these hotels feature a variety of services, and offer distinguished style and comfort.

    Experience comfort and relaxation in the heart of Waikiki at this hotel while enjoying an exceptional vacation value.

    • Partial Ocean View
    • Includes EXCLUSIVE 3-Day FREE mid-size car rental

    3 nights with flight from $720+

    Portland, Oregon (PDX) departures, valid for travel 03/02/20 - 03/05/20
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  • Outrigger Waikiki Beach Resort
    Outrigger Waikiki Beach Resort
    Waikiki, Oahu Our 4.5-Star classification designates those properties with well-appointed, deluxe accommodations, extensive amenities and comprehensive guest services. Expect attention to detail and a warm and hospitable staff ready to cater to your needs. These superb properties offer a truly refined getaway. Half star indicates that the hotel/resort meets all criteria of the designated rating and exceeds in certain areas.

    “Where the Beach Comes Alive” Our extended ohana (family) will discover local beach and surf culture at this hotel on Waikiki Beach.
    • City View Queen
    • Includes EXCLUSIVE 3-Day FREE mid-size car rental

    3 nights with flight from $721+

    Portland, Oregon (PDX) departures, valid for travel 03/02/20 - 03/05/20
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  • Moana Surfrider, A Westin Resort & Spa
    Moana Surfrider, A Westin Resort & Spa
    Waikiki, Oahu Our 4.5-Star classification designates those properties with well-appointed, deluxe accommodations, extensive amenities and comprehensive guest services. Expect attention to detail and a warm and hospitable staff ready to cater to your needs. These superb properties offer a truly refined getaway. Half star indicates that the hotel/resort meets all criteria of the designated rating and exceeds in certain areas.

    This legendary resort, "The First Lady of Waikiki," combines turn-of the-century Victorian elegance with modern Westin amenities and luxuries.

    • Historic Banyan
    • 15% spa discount
    • Daily Beach Club access for up to two people per room
    • Includes EXCLUSIVE 3-Day FREE mid-size car rental

    3 nights with flight from $751+

    Portland, Oregon (PDX) departures, valid for travel 03/02/20 - 03/05/20
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  • Outrigger Reef Waikiki Beach Resort
    Outrigger Reef Waikiki Beach Resort
    Waikiki, Oahu Our 4.5-Star classification designates those properties with well-appointed, deluxe accommodations, extensive amenities and comprehensive guest services. Expect attention to detail and a warm and hospitable staff ready to cater to your needs. These superb properties offer a truly refined getaway. Half star indicates that the hotel/resort meets all criteria of the designated rating and exceeds in certain areas.

    "Sharing the Arts & Culture of Hawaii" This distinctive, refined hotel presents a new vision of hospitality, combining timeless traditions with modern elegance.
    • City View King
    • Includes EXCLUSIVE 3-Day FREE mid-size car rental

    3 nights with flight from $758+

    Portland, Oregon (PDX) departures, valid for travel 03/02/20 - 03/05/20
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  • Waikiki Beachcomber by Outrigger
    Waikiki Beachcomber by Outrigger
    Waikiki, Oahu Our 4.5-Star classification designates those properties with well-appointed, deluxe accommodations, extensive amenities and comprehensive guest services. Expect attention to detail and a warm and hospitable staff ready to cater to your needs. These superb properties offer a truly refined getaway. Half star indicates that the hotel/resort meets all criteria of the designated rating and exceeds in certain areas.

    "An Oasis in the Heart of Waikiki" This brand new lifestyle resort which just completed a $35 million modernization offers contemporary comfort, camaraderie and fun.
    • Waikiki View King
    • Includes EXCLUSIVE 3-Day FREE mid-size car rental

    3 nights with flight from $764+

    Portland, Oregon (PDX) departures, valid for travel 03/02/20 - 03/05/20
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  • 'Alohilani Resort Waikiki Beach
    'Alohilani Resort Waikiki Beach
    Waikiki, Oahu Our 4.5-Star classification designates those properties with well-appointed, deluxe accommodations, extensive amenities and comprehensive guest services. Expect attention to detail and a warm and hospitable staff ready to cater to your needs. These superb properties offer a truly refined getaway. Half star indicates that the hotel/resort meets all criteria of the designated rating and exceeds in certain areas.

    Named among the Best Resorts in Hawaii in the 2018 Condé Nast Readers' Choice Awards, This newly renovated family-friendly resort is across from Waikiki Beach within easy walking to nearby shops, restaurants, and attractions.

    • Ocean View King
    • Includes EXCLUSIVE 3-Day FREE mid-size car rental

    3 nights with flight from $834+

    Portland, Oregon (PDX) departures, valid for travel 03/02/20 - 03/05/20
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  • The Ritz-Carlton Residences, Waikiki Beach Hotel
    The Ritz-Carlton Residences, Waikiki Beach Hotel
    Waikiki, Oahu Our 5-Star classification designates those select properties that provide exquisite service and amenities. The discriminating traveler will find the accommodations, ambiance, dining, and staff assistance of the highest caliber. These properties offer the utmost in luxury and will provide an outstanding experience.

    Discover the debut of a new and distinctive resort experience at The Ritz-Carlton Residences, Waikiki Beach featuring stylishly-appointed suites, incomparable ocean views and legendary service.
    • Ocean View
    • Includes EXCLUSIVE 3-Day FREE mid-size car rental

    3 nights with flight from $1158+

    Portland, Oregon (PDX) departures, valid for travel 03/02/20 - 03/05/20
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  • Aulani, A Disney Resort & Spa
    Aulani, A Disney Resort & Spa
    Ko Olina Resort Area, Oahu Our 5-Star classification designates those select properties that provide exquisite service and amenities. The discriminating traveler will find the accommodations, ambiance, dining, and staff assistance of the highest caliber. These properties offer the utmost in luxury and will provide an outstanding experience.

    Inspired by the wonders and traditions of Hawaii, Aulani has been uniquely designed for families.

    • Island Garden View
    • Includes EXCLUSIVE 3-Day FREE mid-size car rental

    3 nights with flight from $1277+

    Portland, Oregon (PDX) departures, valid for travel 03/02/20 - 03/05/20
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Hawaii - Hot Deals FREE 3-Day Hertz Car Rental offer: Valid on new bookings made 01/13/2020 – 03/01/2020 for travel 01/13/2020 – 12/14/2020. Minimum 3 nights’ hotel accommodation at participating resort and roundtrip airfare required. Bookings receive FREE a 3-day midsize car rental; additional car rental days may be added at additional rate. Value of 3-day midsize car rental may be applied to upgraded car classes, but may not be redeemed for cash or discounted off the vacation package price. Age restrictions may apply for car rental.
Rates quoted are per person, based on double occupancy unless otherwise stated. Rates for other travel dates may vary. Rates, terms, conditions and itinerary are subject to availability. Certain restrictions apply. Rates shown include government-imposed fees and taxes. Airline fees for optional services, including, but not limited to, baggage fees, may apply. Airline tickets are non-refundable and subject to airline change/cancellation penalties and rules, including pre-flight notification deadlines. Fees and policies vary among airlines and are subject to change without notice. Please contact the airline directly for details and answers to specific questions you may have. Additional restrictions apply. Advertised rates do not include any applicable daily resort or facility fees payable directly to the hotel operator at check-out; such fee amounts will be advised at the time of booking. Where applicable, kids stay free in same room as adults using existing bedding. Occupancy limits apply. Where applicable, kids eat free with full paying adult. Not responsible for errors or omissions. [Pleasant Holidays acts only as an agent for the various travel providers shown above.]